Altitude with Cities

I've been making some cities here and there. I'm not spending a lot of time on them since they will take up no more than two gaming sessions, so they aren't that great. But anyway, the point is I'm trying to figure out how to do altitude. In my first one the city was in a sandy/rocky valley. I wasn't too upset with how it turned out, which just involved three layers of contours. It could have been better, but I just went on with it.

Then I tried making a walled town sitting on top of a grassy hill. I tried fading darker, I tried fading lighter... blah. It's good enough for how long I need it, but I think this is going to continue to be an issue.

http://www.tyrion.net/gaming/Jifarah.pdf
http://tyrion.net/Hilltop.BMP

I'm an engineer. Art isn't my thing. I just don't know how to make it look like a hill from directly overhead. Any help?

Thanks

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